Of 6-trityl-/3-d-glucose

Hoschele62 has recently treated 6-0-trityl-/3-D-glucose tetraacetate with zinc chloride to form tri-0-acetyl-l,6-anhydro-/3-D-glucopyranose. The course of reaction undoubtedly was analogous to that described above for the formation of the latter substance from 1,2,3,4-tetra-0-acety 1-/3-d-glucose.33... 

Proof of Constitution.—The method of synthesis from methyl 6-trityl-ajS-D-glucofuranoside furnished strong evidence that the trimethyl-D-glucose isolated by Smith121 was substituted at positions 2, 3 and 5. This conclusion was confirmed by the observations (a) that the trimethyl-gluconolactone, produced when the sugar was oxidized with bromine... 

Cleavage of a trUyl ether. The trityl ether (2) [6-0-trityl-l,2,3,4-tetra-0-acetyl-/3-D-glucose] was detritylated by adding a saturated solution of dry hydrogen bromide... 

The fructofurano-oxazoline 16 was obtained by reaction of 1,6-di-O-trityl-D-fructosc with cyanamide, and used in the construction of nucleoside analogues (see Chapter 20). The imidazoline 17 formed through solvent incorporation when l,3,4,6-tetra-0-acetyl-2-allyloxycarbonylamino-2-deoxy- 3-D-glucose was used as a glycosylating agent in acetonitrile. Synthesis of the cross-conjugated betaines 18 from glucosylamine has been reported. ... 

Rennie (49), working in my laboratory, succeeded in converting d-glucose into 4-deoxy-D-Jct/Zo-hexose, albeit with considerable difficulty, by the following sequence of reactions which incorporate mercaptalation of the carbonyl group and reductive desulfurization of the dithiol 1 2 D-glucose methyl 2,3-di-0-benzyl-6-0-trityl-a-D-glucopyranoside - ... 

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